Herbicidal pyrimidine and triazine sulfonamides

ABSTRACT

N-(heterocyclicaminocarbonyl)arylsulfonamides and thienylsulfonamides in which the heterocyclic radical is substituted in one position by a methyl or methoxy radical and in another by a substituted alkoxy or alkylthio radical; e.g., N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide and N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

BACKGROUND OF THE INVENTION

This invention relates to novel N-(heterocyclicaminocarbonyl)arylsulfonamides and N-(heterocyclicaminocarbonyl)thienylsulfonamides in which the heterocyclic radical is substituted in one position by a methyl or methoxy radical and in another by a substituted alkoxy or alkylthio radical. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g., plant growth regulants and herbicides.

U.S. application Ser. Nos. 824,805 filed Aug. 15, 1977 and 840,389, filed Oct. 6, 1977 disclose, inter alia, compounds of the following formula as herbicides: ##STR1## In the former R is a radical having the formula: ##STR2## and in the latter, a radical having the formula: ##STR3## In each of those applications,

R₁ may be ##STR4## R₃ may be chlorine, bromine, fluorine, nitro, methyl, methoxy, trifluoromethyl or ##STR5##

n is 0, 1 or 2;

R₄, R₅, R₆ and R₇ may each be hydrogen, fluorine, chlorine, bromine, or methyl; moreover in each application, each of R₅, R₆ and R₇ may be methoxy. In each application, X may be alkoxy of 1-3 carbon atoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; Z is methyl or methoxy; and W is oxygen or sulfur.

U.S. application Ser. No. 840,167, filed Oct. 6, 1977, discloses, inter alia, compounds having the following formula as herbicides: ##STR6## wherein

each of R₁ and R₂ may be hydrogen or methyl;

R₃ is ##STR7##

X may be alkoxy of one to three carbons, CF₃, CH₃ S--, CH₃ OCH₂ -- or CH₃ OCH₂ CH₂ O--;

Y is CH₃ or OCH₃ ; and

Z is CH or N.

U.S. application Ser. No. 910,965, filed May 30, 1978, discloses, inter alia, compounds of the following formula as herbicides: ##STR8## wherein ##STR9## is an acid, salt, ester or amide radical;

R₁ may be ##STR10##

R₂ may be hydrogen, chlorine, bromine, fluorine, nitro, methyl, methoxy or methylthio; R₃ is hydrogen, chlorine, bromine or methyl;

R₄ and R₅ are independently hydrogen or methyl;

W is oxygen or sulfur;

X may be methyl or methoxy;

Y may be --OCH₂ CF₃, --O(CH₂)₂ OCH₃, --O(CH₂)₂ OC₂ H₅, --O(CH₂)₃ OCH₃, --O(CH₂)₃ OC₂ H₅, --OCH₂ CO₂ CH₃, --OCH₂ CO₂ C₂ H₅, ##STR11## --O(CH₂)₂ CO₂ CH₃, --O(CH₂)₂ CO₂ C₂ H₅ ; --S(CH₂)₂ OCH₃, --S(CH₂)₂ OC₂ H₅, --SCH₂ CO₂ CH₃, --SCH₂ CO₂ C₂ H₅, ##STR12## --S(CH₂)₂ CO₂ CH₃, or S(CH₂)₂ CO₂ C₂ H₅ ; and Z is CH or N.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need still exists for effective herbicides.

SUMMARY OF THE INVENTION

According to this invention, there are provided novel compounds of Formula I and their agriculturally suitable salts, suitable agricultural compositions containing them and methods of using them as plant growth regulants pre-emergence and post-emergence herbicides, both general and selective: ##STR13## wherein

R is ##STR14##

R₁ and R₂ are independently H or CH₃ ;

R₃ is --CH₂ CF₃, --CH₂ CH₂ OR₆, --CH₂ CO₂ R₆, ##STR15## --CH₂ CH₂ --CH₂ OR₆ or --CH₂ CH₂ CO₂ R₆ ;

R₄ is Cl, Br, F, NO₂, CH₃, --OCH₃, CF₃, or ##STR16##

R₅ is H, Cl, Br, F, CH₃ or --OCH₃ ;

R₆ is CH₃ or CH₂ CH₃ ;

n is 0, 1 or 2;

X is CH₃ or --OCH₃ ;

W and Y are independently O or S; and

Z is CH or N;

provided that when

(a) R₃ is --CH₂ CF₃, Y is O; and

(b) R₃ is --CH₂ CH₂ OCH₃ and either or both of R₁ and R₂ is CH₃, Y is S.

Preferred in order of increasing activity and/or increasingly favorable cost are:

(1) Compounds of the generic scope wherein R₁ and R₂ are H and W is O;

(2) Compounds of preference (1) wherein R is ##STR17##

(3) Compounds of preference (2) wherein R₅ is H or Cl;

(4) Compounds of preference (3) wherein R₄ is Cl or NO₂ ;

(5) Compounds of preference (4) wherein R₅ is H.

More preferred in order of increasing activity and/or increasingly more favorable cost are:

(6) Compounds of the generic scope wherein Y is O;

(7) Compounds of preference (1) wherein Y is O;

(8) Compounds of preference (2) wherein Y is O;

(9) Compounds of preference (3) wherein Y is O;

(10) Compounds of preference (4) wherein Y is O;

(11) Compounds of preference (5) wherein Y is O.

Specifically preferred for their exceptional activity and/or very favorable cost are:

N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide,

N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide.

Synthesis

As shown in Equation 1, the compounds of Formula I can be prepared by reacting an appropriately substituted sulfonyl isocyanate or isothiocyanate of Formula II with an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of Formula III; R₂, R₃, W, X, Y and Z being as previously defined. ##STR18##

The reaction of Equation 1 is best carried out in inert aprotic organic solvents such as methylene chloride, tetrahydrofuran or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate or isothiocyanate II to a stirred suspension of heterocyclic amine III. Since such isocyanates and isothiocyanates usually are liquids, their addition can be easily controlled. The reaction is generally exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallizes from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as 1-chlorobutane or ethyl ether, and filtration.

As shown in Equation 2, the compounds of Formula I, wherein R₁ is H and R₂ is CH₃, can be prepared by reacting an appropriately substituted sulfonyl isocyanate or isothiocyanate of Formula II with an appropriate 2-methylaminopyrimidine or 2-methylamino-1,3,5-triazine of Formula III; R, R₃, W, X, Y and Z being as previously defined. ##STR19## The reaction is carried out as is described for that of Equation 1.

Compounds of Formula I wherein R₁ is methyl, can be prepared by methylation of the salts of compounds of Formula I wherein R₁ is H, as shown in Equation 3; R, R₂, R₃, W, X, Y and Z being as previously defined and M is a metal cation and Q an anion, such as halide or sulfate. ##STR20##

The reaction of Equation 3 is best carried out in aprotic organic solvents such as tetrahydrofuran, dimethylformamide, or dimethylacetamide, at ambient pressure and temperature. Alkylating agents such as dimethyl sulfate, or methyl iodide can be employed. The desired product can be isolated by pouring the reaction mixture into water and filtering off the precipitated solid.

Alternatively, compounds of Formula I wherein R₁ is methyl, can be prepared by the reaction of an appropriately substituted sulfonyl-N-methylcarbamyl chloride or sulfonyl-N-methylcarbamylthioic chloride of Formula IV with an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine of Formula III; as shown in Equation 4; R₂, R₁, R, X, Y, and Z being as previously defined. ##STR21##

The preparation of ureas from amines and carbamyl chlorides or carbamylthioic chlorides is well known to the art. The reaction can best be carried out by adding equivalent amounts of the chloride IV and amine III to an inert organic solvent, such as tetrahydrofuran, xylene, or methylene chloride, in the presence of acid acceptor, such as triethylamine, pyridine, or sodium carbonate employing temperatures from 20°-130°. Soluble products can be isolated by filtering off precipitated salts and concentration of the filtrate. Insoluble products can be filtered off and washed free of salts with water.

The intermediate chlorides IV can be prepared by phosgenation or thiophosgenation of N-methylsulfonamide salts. The sulfonamide salt is added to an excess of phosgene or thiophosgene in an inert organic solvent, such as tetrahydrofuran, toluene, or xylene, whereupon the chloride IV can be isolated or reacted in situ with the amine III after removal of the excess phosgene or thiophosgene.

The preparation of agriculturally suitable salts of the compounds of Formula I, as well as starting materials and intermediates for said compounds is disclosed in U.S. applications Ser. No. 824,805 filed Aug. 15, 1977 and Ser. No. 840,389 filed Oct 6, 1977, the contents of which are incorporated herein by reference.

The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade.

EXAMPLE 1 N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-chlorobenzenesulfonamide

To a dry stirred solution of 18.3 parts of 2-amino-4-(2-methoxyethoxy)-6-methylpyrimidine in 300 parts of methylene chloride at ambient temperature and pressure was added 22 parts of 2-chlorobenzenesulfonylisocyanate. The mixture was stirred for 2 hours and then the methylene chloride was removed under reduced pressure. The resulting solid was triturated with 1-chlorobutane and filtered to yield 35 parts of N-[[4-(2-methoxyethoxy)-6-methylpyrimidine-2-yl]aminocarbonyl]-2-chlorobenzenesulfonamide, m.p. 130°-140° C. The product showed characteristic absorption bands in the infrared spectrum.

By using the procedure of Example 1 with an equivalent amount of appropriate 2-aminopyrimidines or 2-amino-1,3,5-triazines and appropriately substituted benzenesulfonyl isocyanates or isothiocyanates, the compounds of Table 1 can be prepared.

                  Table 1-A                                                        ______________________________________                                          ##STR22##                                                                     R.sub.4                                                                               R.sub.5  X       YR.sub.3      m.p. °C.                          ______________________________________                                         Cl     H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    Cl     H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                           160-163                                  Cl     H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                                                                  157-160                                  Cl     H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                     Cl     H        CH.sub.3                                                                                ##STR23##    178-191                                  Cl     H        CH.sub.3                                                                                ##STR24##    114-122                                  Cl     H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                   Cl     H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            Cl     H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        103-115                                  Br     H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                           Br     H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     Br     H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                            F      H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    F      H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     F      H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                            NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                  NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                                                                 95-98                                    NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                           192-194                                  NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                                                                  155-165                                  NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                     NO.sub.2                                                                              H        CH.sub.3                                                                                ##STR25##    175-179                                  NO.sub.2                                                                              H        CH.sub.3                                                                                ##STR26##                                             NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.5                   NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            NO.sub.2                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5           CH.sub.3                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                           CH.sub.3                                                                              H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     CH.sub.3                                                                              H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                     CH.sub.3                                                                              H        CH.sub.3                                                                                ##STR27##                                             CH.sub.3                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            OCH.sub.3                                                                             H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    OCH.sub.3                                                                             H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     OCH.sub.3                                                                             H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                            OCH.sub.3                                                                             H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                   CF.sub.3                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                           CF.sub.3                                                                              H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     CF.sub.3                                                                              H        CH.sub.3                                                                                ##STR28##                                             CF.sub.3                                                                              H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                   SCH.sub.3                                                                             H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    SCH.sub.3                                                                             H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                      ##STR29##                                                                            H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                      ##STR30##                                                                            H        CH.sub.3                                                                                ##STR31##                                              ##STR32##                                                                            H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5             ##STR33##                                                                            H        CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                            ##STR34##                                                                            H        CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                      ##STR35##                                                                            H        CH.sub.3                                                                               OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                     Cl     5-Cl     CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                                                                 151-155                                  Cl     5-Cl     CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                                                           162.5-165                                Cl     5-Cl     CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                                                                  182-186                                  Cl     5-Cl     CH.sub.3                                                                                ##STR36##                                             Cl     5-Cl     CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                  Cl     3-Cl     CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                           Cl     5-Br     CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    Cl     5-F      CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     Cl     5-CH.sub.3                                                                              CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                            Cl     5-OCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     Cl     6-Cl     CH.sub.3                                                                               OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                     Br     5-Br     CH.sub.3                                                                                ##STR37##                                             Cl     5-Cl     OCH.sub.3                                                                              OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                     Cl     5-Cl     OCH.sub.3                                                                              OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    F      5-F      CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            NO.sub.2                                                                              5-Cl     CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                           NO.sub.2                                                                              6-Cl     CH.sub.3                                                                               OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                     NO.sub.2                                                                              3-CH.sub.3                                                                              CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                           NO.sub.2                                                                              5-OCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     CH.sub.3                                                                              5-CH.sub.3                                                                              CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                           CH.sub.3                                                                              5-Cl     CH.sub.3                                                                                ##STR38##                                             OCH.sub.3                                                                             5-OCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    CF.sub.3                                                                              5-Cl     CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     CF.sub.3                                                                              5-Cl     CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3                            SCH.sub.3                                                                             5-Cl     CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                            ##STR39##                                                                            5-Cl     CH.sub.3                                                                               OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                    ##STR40##                                                                            5-OCH.sub.3                                                                             CH.sub.3                                                                               OCH.sub.2 CF.sub.3                                     Cl     H        CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                          127-130                                  Cl     H        CH.sub.3                                                                               SCH.sub.2 CO.sub.2 CH.sub.3                            Cl     5-Cl     CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                          131-150                                  Cl     5-Cl     CH.sub.3                                                        ##STR41##                                                                     Br     H        CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OCH.sub.3                           F      H        CH.sub.3                                                                               SCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5            NO.sub.2                                                                              H        CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OC.sub.2 H.sub. 5                   NO.sub.2                                                                              H        CH.sub.3                                                                               SCH.sub.2 CO.sub.2 C.sub.2 h.sub.5                     CH.sub.3                                                                              H        CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OCH.sub.3                           OCH.sub.3                                                                             H        CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    CF.sub.3                                                                              H        CH.sub.3                                                                                ##STR42##                                             CF.sub.3                                                                              5-Cl     CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OCH.sub.3                            ##STR43##                                                                            H        CH.sub.3                                                                               SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    Cl     H        OCH.sub.3                                                                              OCH.sub.2 CH.sub.2 OCH.sub.3                           Cl     5-Cl     OCH.sub.3                                                                              OCH.sub.2 CF.sub.3                                     NO.sub.2                                                                              H        OCH.sub.3                                                                              OCH.sub.2 CO.sub.2 CH.sub.3                            CF.sub.3                                                                              H        OCH.sub.3                                                                              OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                    CH.sub.3                                                                              H        OCH.sub.3                                                                              S-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   OCH.sub.3                                                                             H        OCH.sub.3                                                                              OCH.sub.2 CF.sub.3                                      ##STR44##                                                                            H        OCH.sub.3                                                                              OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                   ______________________________________                                    

                  Table 1-B                                                        ______________________________________                                          ##STR45##                                                                     R.sub.4   R.sub.5   X        YR.sub.3                                          ______________________________________                                         Cl        H         CH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3                      Cl        5-Cl      CH.sub.3 OCH.sub.2 CF.sub.3                                NO.sub.2  H         CH.sub.3 OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                NO.sub.2  H         CH.sub.3 OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3              CH.sub.3  H         CH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3             OCH.sub.3 H         CH.sub.3 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5               SCH.sub.3 H         CH.sub.3                                                                                 ##STR46##                                         ##STR47##                                                                               H         CH.sub.3 SCH.sub.2 CO.sub.2 CH.sub.3                       CF.sub.3  H         CH.sub.3 SCH.sub.2 CH.sub.2 OCH.sub.3                      F         H         OCH.sub.3                                                                               OCH.sub.2 CF.sub.3                                Br        H         OCH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3                       ##STR48##                                                                               H         OCH.sub.3                                                                                ##STR49##                                        ______________________________________                                    

                  Table 1-C                                                        ______________________________________                                          ##STR50##                                                                     R.sub.4 R.sub.5  X         YR.sub.3                                            ______________________________________                                         Cl      H        CH.sub.3  OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                 Cl      H        CH.sub.3  OCH.sub.2 CF.sub.3                                  Cl      5-Cl     CH.sub.3  OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                  Cl      5-Cl     CH.sub.3                                                                                  ##STR51##                                          NO.sub.2                                                                               H        CH.sub.3  OCH.sub.2 CH.sub.2 OCH.sub.3                        NO.sub.2                                                                               H        CH.sub.3  OCH.sub.2 CF.sub.3                                  Br      H        OCH.sub.3 SCH.sub.2 CO.sub.2 CH.sub.3                         CH.sub.3                                                                               H        OCH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5        ______________________________________                                    

                  Table 1-D                                                        ______________________________________                                          ##STR52##                                                                     R.sub.4 R.sub.5  X         YR.sub.3                                            ______________________________________                                         Cl      H        CH.sub.3  OCH.sub.2 CH.sub.2 OCH.sub.3                        Cl      H        CH.sub.3  OCH.sub.2 CF.sub.3                                  Cl      5-Cl     CH.sub.3  OCH.sub.2 CO.sub.2 CH.sub.3                         NO.sub.2                                                                               H        CH.sub.3                                                                                  ##STR53##                                          NO.sub.2                                                                               H        CH.sub.3  SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                 NO.sub.2                                                                               H        CH.sub.3  OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                 NO.sub.2                                                                               H        OCH.sub.3 OCH.sub.2 CF.sub.3                                  Br      H        CH.sub.3  OCH.sub.2 CH.sub.2 OCH.sub.3                        SCH.sub.3                                                                              H        OCH.sub.3                                                                                 ##STR54##                                           ##STR55##                                                                             H        OCH.sub.3 S CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                 ______________________________________                                    

EXAMPLE 2 Methyl [6-methyl-2-[(2-thienylsulfonyl)aminocarbonylamino]pyrimidin-4-yloxy]acetate

To a dry stirred solution of 18 parts of methyl (2-amino-6-methylpyrimidin-4-yloxy)acetate in 300 parts of methylene chloride at ambient temperature was added 20 parts of 2-thiophenesulfonylisocyanate. The solution was allowed to stand for 3 hours and was then poured onto ice. The pH of the aqueous layer was adjusted to 11 with sodium hydroxide solution and the methylene chloride layer was separated therefrom. The aqueous layer was neutralized with aqueous hydrochloric acid and then extracted with methylene chloride. The extract was dried and stripped of solvent to yield 8 parts of methyl [6-methyl-2-[(2-thienylsulfonyl)aminocarbonylamino]pyrimidin-4-yloxy]acetate, m.p. 114°-120°.

By using the procedure of Example 2 with equivalent amounts of appropriate 2-aminopyrimidines or 2-amino-1,3,5-triazines and 2-thiophenesulfonylisocyanates or isothiocyanates, the compounds of Table 2 can be prepared.

                  Table 2-A                                                        ______________________________________                                          ##STR56##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3        OCH.sub.2 CH.sub.2 OCH.sub.3                                   CH.sub.3        OCH.sub.2 CF.sub.3                                             CH.sub.3                                                                                        ##STR57##                                                     CH.sub.3        OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                    CH.sub.3        OCH.sub.2 CH.sub.2 OCH.sub.3                                   CH.sub.3        SCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                          CH.sub.3        SCH.sub.2 CO.sub.2 CH.sub.3                                    OCH.sub.3       OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            OCH.sub.3       OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                          ______________________________________                                    

                  Table 2-B                                                        ______________________________________                                          ##STR58##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3        OCH.sub.2 CH.sub.2 OCH.sub.2                                   CH.sub.3        OCH.sub.2 CF.sub.3                                             CH.sub.3        OCH.sub.2 CO.sub.2 CH.sub.3                                    CH.sub.3                                                                                        ##STR59##                                                     OCH.sub.3       OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                           OCH.sub.3       OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            OCH.sub.3       OCH.sub.2 CF.sub.3                                             CH.sub.3        OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                             CH.sub.3        SCH.sub.2 CH.sub.2 OCH.sub.3                                   CH.sub.3        SCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                           ______________________________________                                    

                  Table 2-C                                                        ______________________________________                                          ##STR60##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3        OCH.sub.2 CH.sub.2 OCH.sub.3                                   CH.sub.3        OCH.sub.2 CF.sub.3                                             CH.sub.3        OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                             CH.sub.3                                                                                        ##STR61##                                                     CH.sub.3        OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5                    CH.sub.3        OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            OCH.sub.3       OCH.sub.2 CO.sub.2 CH.sub.3                                    OCH.sub.3       OCH.sub.2 CF.sub.3                                             OCH.sub.3       OCH.sub.2 CH.sub.2 OCH.sub.3                                   OCH.sub.3       SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            CH.sub.3        SCH.sub.2 CO.sub.2 CH.sub.3                                    ______________________________________                                    

                  Table 2-D                                                        ______________________________________                                          ##STR62##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3        OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            CH.sub.3        OCH.sub.2 CF.sub.3                                             CH.sub.3                                                                                        ##STR63##                                                     OCH.sub.3       OCH.sub.2 CF.sub.3                                             OCH.sub.3       OCH.sub.2 CO.sub.2 CH.sub.3                                    OCH.sub.3       SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            OCH.sub.3       SCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                             CH.sub.3                                                                                        ##STR64##                                                     CH.sub.3        SCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                           ______________________________________                                    

By using the procedure of Equation 2 with an equivalent amount of appropriate 2-methylaminopyrimidines or 2-methylamino-1,3,5-triazines and appropriately substituted benzenesulfonylisocyanates or isothiocyanates, the compounds of Table 3 can be prepared. For example, to a dry stirred solution of 19.7 parts of 2-methylamino-4-(2-methoxyethylthio)-6-methylpyrimidine in 300 parts of methylene chloride at ambient temperature is added 22.8 parts of 2-nitrobenzenesulfonylisocyanate. That mixture is stirred and refluxed for 4 hours, and then the methylene chloride is removed under reduced pressure. The resulting solid is triturated with 1-chlorobutane to yield N-[N-[4-(2-methoxyethylthio)-6-methylpyrimidin-2-yl]-N-methylaminocarbonyl]-2-nitrobenzenesulfonamide.

                  Table 3-A                                                        ______________________________________                                          ##STR65##                                                                     R.sub.4 R.sub.5  X         YR.sub.3                                            ______________________________________                                         Cl      H        CH.sub.3  SCH.sub.2 CH.sub.2 OCH.sub.3                        Cl      H        CH.sub.3  OCH.sub.2 CF.sub.3                                  Cl      5-Cl     CH.sub.3  OCH.sub.2 CO.sub.2 CH.sub.3                         NO.sub.2                                                                               H        CH.sub.3  OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5         NO.sub.2                                                                               H        OCH.sub.3 SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                 Br      H        CH.sub.3  SCH.sub.2 CO.sub.2 CH.sub.3                         CH.sub.3                                                                               H        CH.sub.3                                                                                  ##STR66##                                          ______________________________________                                    

                  Table 3-B                                                        ______________________________________                                          ##STR67##                                                                     R.sub.4 R.sub.5  X         YR.sub.3                                            ______________________________________                                         Cl      H        CH.sub.3  SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                 Cl      H        CH.sub.3  OCH.sub.2 CF.sub.3                                  Cl      5-Cl     CH.sub.3  SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                 NO.sub.2                                                                               H        CH.sub.3  OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                  Br      H        CH.sub.3  OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                OCH.sub.3                                                                              H        OCH.sub.3 OCH.sub.2 CF.sub.3                                  ______________________________________                                    

                  Table 3-C                                                        ______________________________________                                          ##STR68##                                                                     R.sub.4 R.sub.5  X         YR.sub.3                                            ______________________________________                                         Cl      H        CH.sub.3  SCH.sub.2 CH.sub.2 OCH.sub.3                        Cl      H        CH.sub.3  OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                  Cl      5-Cl     CH.sub.3  OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3               NO.sub.2                                                                               H        CH.sub.3  OCH.sub.2 CF.sub.3                                  NO.sub.2                                                                               H        OCH.sub.3 OCH.sub.2 CF.sub.3                                  ______________________________________                                    

                  Table 3-D                                                        ______________________________________                                          ##STR69##                                                                     R.sub.4                                                                               R.sub.5  X         YR.sub.3                                             ______________________________________                                         Cl     H        CH.sub.3  OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                  Cl     H        CH.sub.3                                                                                  ##STR70##                                           Cl     5-Cl     OCH.sub.3 OCH.sub.2 CF.sub.3                                   NO.sub.2                                                                              H        CH.sub.3  SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                  NO.sub.2                                                                              H        OCH.sub.3 OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2 H.sub.5          Br     H        CH.sub.3  OCH.sub.2 CF.sub.3                                   ______________________________________                                    

EXAMPLE 3 N-[N-[4-(2,2,2-Trifluoroethoxy)-6-methylpyrimidin-2-yl]-N-methylaminocarbonyl]-2-thiophenesulfonamide

To a dry stirred solution of 22.1 parts of 2-methylamino-4-(2,2,2-trifluorethoxy)-6-methylpyrimidine in 250 parts of methylene chloride at ambient temperature was added 18.9 parts of 2-thiophenesulfonyl isocyanate. That mixture was stirred and refluxed for 2 hours. The methylene chloride was removed under reduced pressure, and the resulting solid was triturated with toluene to yield 19 parts of N-[N-[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]-N-methylaminocarbonyl]-2-thiophenesulfonamide.

By using the procedure of Example 3 with equivalent amounts of appropriate 2-methylaminopyrimidines or 2-methylamino-1,3,5-triazines and 2-thiophenesulfonyl isocyanates or isothiocyanates, the compounds of Table 4 can be prepared.

                  Table 4-A                                                        ______________________________________                                          ##STR71##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3        SCH.sub.2 CH.sub.2 OCH.sub.3                                   CH.sub.3        OCH.sub.2 CO.sub.2 CH.sub.3                                    CH.sub.3        OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                           CH.sub.3        SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            OCH.sub.3       OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            OCH.sub.3       OCH.sub.2 CF.sub.3                                             OCH.sub.3                                                                                       ##STR72##                                                     ______________________________________                                    

                  Table 4-B                                                        ______________________________________                                          ##STR73##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3        OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            CH.sub.3        OCH.sub.2 CF.sub.3                                             CH.sub.3        OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                          OCH.sub.3       SCH.sub.2 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                   OCH.sub.3       SCH.sub.2 CO.sub.2 C.sub.2 H.sub.5                             ______________________________________                                    

                  Table 4-C                                                        ______________________________________                                          ##STR74##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3        SCH.sub.2 CH.sub.2 OCH.sub.3                                   CH.sub.3        OCH.sub.2 CF.sub.3                                             CH.sub.3        OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                           OCH.sub.3       SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                            ______________________________________                                    

                  Table 4-D                                                        ______________________________________                                          ##STR75##                                                                     X               YR.sub.3                                                       ______________________________________                                         CH.sub.3                                                                                        ##STR76##                                                     CH.sub.3        SCH.sub.2 CO.sub.2 CH.sub.3                                    CH.sub.3        SCH.sub.2 CH.sub.2 OCH.sub.3                                   OCH.sub.3       OCH.sub.2 CF.sub.3                                             ______________________________________                                    

N-methyl compounds of this invention can be prepared in accordance with the procedures described above. For example, the methylation procedure of Equation 3 can be used as follows:

An equivalent amount of sodium hydride (50% mineral oil dispersion) is added to a solution of N-[[4-(2-methoxyethylthio)-6-methylpyrimidin-2-yl]aminocarbonyl]-2,5-dichlorobenzenesulfonamide in dimethylformamide under a nitrogen atmosphere. After hydrogen evolution ceases, an equivalent amount of dimethylsulfate is added. After stirring for 12 hours the reaction mixture is poured into a large volume of water. The resulting precipitate is filtered to yield N-[[4-(2-methoxyethylthio)-6-methylpyrimidin-2-yl]aminocarbonyl]-2,5-dichloro-N-methylbenzenesulfonamide.

Likewise, compounds of this invention wherein both of the urea nitrogens are methylated can be prepared by the procedure of Equation 4 as follows:

To 18 parts of N-[(2-chlorophenyl)sulfonyl]-N-methylcarbamyl chloride in 300 parts of tetrahydrofuran containing 10 parts of triethylamine is added 22 parts of 2-methylamino-4-(2,2,2-trifluoroethoxy)-6-methylpyrimidine. After stirring at reflux for 10 hours, the precipitated salts are filtered off and the filtrate is concentrated to yield N-[N-[4-(2,2,2,-trifluoroethoxy)-6-methylpyrimidin-2-yl]-N-methylaminocarbonyl]-2-chloro-N-methylbenzenesulfonamide.

By using an appropriate N-heterocyclic-N-aminocarbonylbenzenesulfonamide in the foregoing methylation procedure, the compounds of Table 5 can be prepared. Alternatively, by using an appropriate carbamylchloride and an appropriate methylaminoheterocycle with the above-described procedure, the compounds of Table 5 can be prepared.

                  Table 5-A                                                        ______________________________________                                          ##STR77##                                                                     R.sub.2                                                                               R.sub.4  R.sub.5  X      YR.sub.3                                       ______________________________________                                         H      Cl       H        CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                   H      Cl       H        CH.sub.3                                                                              OCH.sub.2 CF.sub.3                             H      Cl       H        CH.sub.3                                                                              OCH.sub.2 CO.sub.2 CH.sub.3                    H      Cl       5-Cl     CH.sub.3                                                                              OCH.sub.2 CH.sub.2 CO.sub.2 C.sub.2                                            H.sub.5                                        H      NO.sub.2 H        CH.sub.3                                                                              OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            H      NO.sub.2 H        CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            H      NO.sub.2 H        CH.sub.3                                                                               ##STR78##                                     H      NO.sub.2 H        OCH.sub.3                                                                             SCH.sub.2 CO.sub.2 CH.sub.3                    H      Br       5-Cl     OCH.sub.3                                                                             OCH.sub.2 CF.sub.3                             CH.sub.3                                                                              CH.sub.3 H        CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                   CH.sub.3                                                                              Cl       H        CH.sub.3                                                                              OCH.sub.2 CO.sub.2 CH.sub.3                    CH.sub.3                                                                              Cl       5-Cl     OCH.sub.3                                                                             OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5            CH.sub.3                                                                              NO.sub.2 H        CH.sub.3                                                                              OCH.sub.2 CF.sub.3                             CH.sub.3                                                                              NO.sub.2 H        CH.sub.3                                                                               ##STR79##                                     ______________________________________                                    

                  Table 5-B                                                        ______________________________________                                          ##STR80##                                                                     R.sub.2                                                                              R.sub.4   R.sub.5 X      YR.sub.3                                        ______________________________________                                         H     Cl        H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                    H     Cl        5-Cl    CH.sub.3                                                                              OXCH.sub.2 CF.sub.3                             H     NO.sub.2  H       CH.sub.3                                                                              OCH.sub.2 CO.sub.2 CH.sub.3                     H     NO.sub.2  H       CH.sub.3                                                                              SCH.sub.2 CO.sub.2 CH.sub.3                     H     NO.sub.2  H       OCH.sub.3                                                                              ##STR81##                                      CH.sub.3                                                                             OCH.sub.3 H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                    CH.sub.3                                                                             SCH.sub.3 H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             CH.sub.3                                                                              ##STR82##                                                                               H       OCH.sub.3                                                                             OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3           CH.sub.3                                                                             NO.sub.2  H       CH.sub.3                                                                              OCH.sub.2 CF.sub.3                              ______________________________________                                    

By using an appropriately substituted N-methyl-N-phenylsulfonylthiocarbamyl chloride and an appropriately substituted 2-aminopyrimidine or 2-amino-1,3,5-triazine the compounds of Table 6 can be made in accordance with the procedure exemplified above.

                  Table 6-A                                                        ______________________________________                                          ##STR83##                                                                     R.sub.2                                                                              R.sub.4  R.sub.5 X      YR.sub.3                                         ______________________________________                                         H     Cl       H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                     H     Cl       5-Cl    CH.sub.3                                                                              OCH.sub.2 CF.sub.3                               H     NO.sub.2 H       CH.sub.3                                                                              OCH.sub.2 CO.sub.2 CH.sub.3                      H     NO.sub.2 H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                     H     CH.sub.3 H       CH.sub.3                                                                              SCH.sub.2 CO.sub.2 C.sub.2 H.sub.5               H     OCH.sub.3                                                                               H       OCH.sub.3                                                                              ##STR84##                                       CH.sub.3                                                                             Br       H       CH.sub.3                                                                              OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5              CH.sub.3                                                                             Cl       5-Cl    CH.sub.3                                                                               ##STR85##                                       CH.sub.3                                                                             NO.sub.2 H       CH.sub.3                                                                              OCH.sub.2 CF.sub.3                               CH.sub.3                                                                             NO.sub.2 H       OCH.sub.3                                                                             OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3            ______________________________________                                    

                  Table 6-B                                                        ______________________________________                                          ##STR86##                                                                     R.sub.2                                                                              R.sub.4  R.sub.5 X      YR.sub.3                                         ______________________________________                                         CH.sub.3                                                                             Cl       H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                     CH.sub.3                                                                             Cl       5-Cl    CH.sub.3                                                                              OCH.sub.2 CO.sub.2 CH.sub.3                      CH.sub.3                                                                             NO.sub.2 H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 OCH.sub.3                     CH.sub.3                                                                             NO.sub.2 H       CH.sub.3                                                                              SCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3             CH.sub.3                                                                             CH.sub.3 H       OCH.sub.3                                                                              ##STR87##                                       H     Br       H       CH.sub.3                                                                              OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5              H     Cl       5-Cl    CH.sub.3                                                                              OCH.sub.2 CF.sub.3                               H     NO.sub.2 H       CH.sub.3                                                                              OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3            H     SCH.sub.3                                                                               H       OCH.sub.3                                                                             SCH.sub. 2 CO.sub.2 C.sub.2 H.sub.5              ______________________________________                                    

The compounds of Table 7 can be prepared by the aforesaid methylation reaction by using an appropriate N-[(1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamide; N-[(pyrimidin-2-yl)aminocarbonyl]-2-thiophenesulfonamide; N-[(1,3,5-triazin-2-yl)aminothioxomethyl]-2-thiophenesulfonamide or N-[(pyrimidin-2-yl)-aminothioxomethyl]-2-thiophenesulfonamide. Alternatively, the compounds of Table 7 can be prepared in accordance with the above-exemplified procedure, using an appropriately substituted N-methyl-N-(2-thienylsulfonyl)carbamyl chloride or thiocarbamyl chloride and an appropriately substituted 2-amino-pyrimidine or 2-amino-1,3,5-triazine.

                  Table 7-A                                                        ______________________________________                                          ##STR88##                                                                     R.sub.2 X           YR.sub.3                                                   ______________________________________                                         H       CH.sub.3    SCH.sub.2 CH.sub.2 OCH.sub.3                               H       CH.sub.3    OCH.sub.2 CF.sub.3                                         H       OCH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3                                H       OCH.sub.3   SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                        H       CH.sub.3    OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                      CH.sub.3                                                                               CH.sub.3                                                                                    ##STR89##                                                 CH.sub.3                                                                               CH.sub.3    OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                       CH.sub.3                                                                               CH.sub.3    OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                        CH.sub.3                                                                               CH.sub.3    OCH.sub.2 CF.sub.3                                         ______________________________________                                    

                  Table 7-B                                                        ______________________________________                                          ##STR90##                                                                     R.sub.2 X           YR.sub.3                                                   ______________________________________                                         H       CH.sub.3    SCH.sub.2 CH.sub.2 OCH.sub.3                               H       CH.sub.3    OCH.sub.2 CF.sub.3                                         H       CH.sub.3    SCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2                      H       OCH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3                                H       OCH.sub.3   SCH.sub.2 CO.sub.2 CH.sub.3                                CH.sub.3                                                                               OCH.sub.3                                                                                   ##STR91##                                                 CH.sub.3                                                                               CH.sub.3    OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                       CH.sub.3                                                                               CH.sub.3    SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                        CH.sub.3                                                                               CH.sub.3                                                                                    ##STR92##                                                 CH.sub.3                                                                               CH.sub.3    OCH.sub.2 CF.sub.3                                         ______________________________________                                    

                  Table 7-C                                                        ______________________________________                                          ##STR93##                                                                     R.sub.2 X           YR.sub.3                                                   ______________________________________                                         H       CH.sub.3    OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                        H       CH.sub.3    OCH.sub.2 CF.sub.3                                         H       CH.sub.3                                                                                    ##STR94##                                                 H       OCH.sub.3   OCH.sub.2 CF.sub.3                                         H       CH.sub.3    OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                       H       CH.sub.3    SCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                      CH.sub.3                                                                               CH.sub.3    SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                        CH.sub.3                                                                               CH.sub.3    SCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3                       CH.sub.3                                                                               OCH.sub.3   SCH.sub.2 CH.sub.2 OCH.sub.3                               CH.sub.3                                                                               OCH.sub.3   OCH.sub.2 CF.sub.3                                         ______________________________________                                    

                  Table 7-D                                                        ______________________________________                                          ##STR95##                                                                     R.sub.2 X           YR.sub.3                                                   ______________________________________                                         H       CH.sub.3    SCH.sub.2 CH.sub.2 OCH.sub.3                               H       OCH.sub.3   OCH.sub.2 CF.sub.3                                         H       CH.sub.3    OCH.sub.2 CO.sub.2 CH.sub.3                                CH.sub.3                                                                               CH.sub.3    SCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                        CH.sub.3                                                                               OCH.sub.3   SCH.sub.2 CO.sub.2 CH.sub.3                                CH.sub.3                                                                               CH.sub.3    OCH.sub.2 CH.sub.2 CH.sub.3 OCH.sub.3                      CH.sub.3                                                                               CH.sub.3                                                                                    ##STR96##                                                 ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of them can be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are used primarily as concentrates which are to be diluted prior to ultimate use. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the approximate proportions set forth in Table 8.

                  Table 8                                                          ______________________________________                                                       Weight Percent*                                                                Active            Surfac-                                                      Ingredient                                                                             Diluent(s)                                                                               tant(s)                                        ______________________________________                                         Wettable Powders                                                                               20-90      0-74     1-10                                       Oil Suspensions,                                                                Emulsions                                                                      (including                                                                     Emulsifiable                                                                   Concentrates)   5-50     40-95     0-15                                       Aqueous Suspensions                                                                            10-50     40-84     1-20                                       Dusts            1-25     70-99     0-5                                        Granules and Pellets                                                                           0.1-95      5-99.9  0-15                                       High Strength Compositions                                                                     90-99      0-10     0-2                                        ______________________________________                                          *Active Ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can be present, depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporated into the formulation, or by tank mixing.

Some typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending, and usually grinding, as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets can be made by spraying the active material on preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 4th Ed., McGraw-Hill, New York, 1963, pp. 8-59ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

Unless indicated otherwise, all parts are by weight in the following examples.

EXAMPLE 4

Wettable Powder

N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide: 90%

dioctyl sodium sulfosuccinate: 0.1%

sodium ligninsulfonate: 1%

synthetic fine silica: 8.9%

The ingredients are blended and ground in a hammer-mill to produce particles almost all of which are below 100 microns in size. That material is sifted through a U.S.S. No. 50 screen and packaged.

EXAMPLE 5

Granule

wettable powder of Example 4: 10%

attapulgite granules (U.S.S. #20-40; 0.84-0.42 mm): 90%

A slurry of wettable powder containing 50% solids is sprayed onto the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 6

Wettable Powder

N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide: 40%

dioctyl sodium sulfosuccinate: 1.5%

sodium ligninsulfonate: 3%

low viscosity methyl cellulose: 1.5%

attapulgite: 54%

The ingredients are thoroughly blended and passed through an air mill to produce an average particle size under 15 microns, reblended, and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) before packaging.

EXAMPLE 7

Granule

wettable powder of Example 6: 25%

gypsum: 64%

potassium sulfate: 11%

The ingredients are blended in a rotating mixer, and water is sprayed onto that blend so as to effect granulation. When most of the granules have reached 1.0 to 0.42 mm (U.S.S. #18to 40sieves) in size, they are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. The resulting granules contain 10% of the active ingredient.

EXAMPLE 8

Wettable Powder

N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide: 80%

sodium alkylnaphthalenesulfonate: 2%

sodium ligninsulfonate: 2%

synthetic amorphorus silica: 3%

kaolinite: 13%

The ingredients are thoroughly blended after grinding in a hammer mill to produce particles essentially all of which are under 100 microns in size; the material is reblended, sifted through a U.S.S. No. 50 sieve and packaged.

EXAMPLE 9

Wettable Powder

N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide: 65%

dodecylphenol polyethylene glycol ether: 2%

sodium ligninsulfonate: 4%

sodium silicoaluminate: 6%

montmorillonite (calcined): 23%

The ingredients are thoroughly blended. The liquid surfactant is added by spraying on the solid ingredients in a blender. After grinding in a hammer mill produce particles almost all of which are below 100 microns in size, the material is reblended, sifted through a U.S.S. #50 sieve (0.3 mm opening) and packaged.

EXAMPLE 10

Oil Suspension

N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide: 25%

polyoxyethylene sorbitol hexaoleate: 5%

highly aliphatic hydrocarbon oil: 70%

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting suspension may be applied directly, but preferably after being extended further with oils or emulsified in water.

EXAMPLE 11

Aqueous Suspension

N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]-aminocarbonyl]-2-nitrobenzenesulfonamide: 25%

hydrated attapulgite: 3%

crude calcium ligninsulfonate: 10%

sodium dihydrogen phosphate: 0.5%

water: 61.5%

The ingredients are ground together in a ball or roller mill until the solid particles have been reduced to sizes under 10 microns, and then packaged.

EXAMPLE 12

Extruded Pellet

N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide: 25%

anhydrous sodium sulfate: 10%

crude calcium ligninsulfonate: 5%

sodium alkylnaphthalenesulfonate: 1%

calcium/magnesium bentonite: 59%

The ingredients are blended, hammer milled and then moistened with about 12% water. The mixture is extruded in the form of cylinders about 3 mm in diameter which are cut to produce pellets about 3 mm long. The pellets may be used directly, after drying, or dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 13

Solution

N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide: 5%

dimethylformamide: 95%

The ingredients are combined and stirred to produce a solution, which can be used for low volume applications.

UTILITY

The compounds of the present invention are highly active herbicides. They have utility for broad spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theatres, parking lots, billboards, highway and railroad structures. By properly selecting rate and time of application, compounds of this invention may be used also to modify plant growth beneficially.

The precise amount of the compound of Formula I to be used in any given situation will vary according to the particular end result desired, the amount of foliage present, the weeds to be controlled, the soil type, the formation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.005 to 20 kg/ha with a preferred range of 0.125 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired.

The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with ureas, such as 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea, and 1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea; the triazines such as 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine; the uracils such as 5-bromo-3-sec-butyl-6-methyluracil; N-(phospono-methyl)glycine; 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione, N,N-dimethyl-2,2-diphenylacetamide; 2,4-dichlorophenoxyacetic acid (and closely related compounds); 4-chloro-2-butynyl-3-3-chlorophenylcarbamate; diisopropylthiolcarbamic acid, ester with 2,3-dichloroallyl alcohol; diisopropylthiolcarbamic acid, S-(2,3,3-trichloroallyl) ester; ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate, 1,2-dimethyl-3,5-diphenylpyrazolium methylsulfate; methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate; 4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one; 3-isopropyl-1H-2,1,3-benzothiodiazin(4)-3H-one 2,2-dioxide; α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine; 1,1'-dimethyl-4,4'-bipyridinium ion; monosodium methanearsonate; and 2-chloro-2',6'-diethyl(methoxymethyl)acetanilide.

The activity of the compounds of this invention was discovered in greenhouse tests. The tests are described and the data resulting from them are shown below.

0=no effect

10=maximum effect

B=burn

C=chlorosis or necrosis

D=defoliation

E=emergence inhibition

G=growth retardation

H=formative effects

S=albinism

U=unusual pigmentation

6Y=abscised buds or flowers

TEST PROCEDURE A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, and wheat, as well as nutsedge tubers (Cyperus rotundus), were planted in a growth medium and treated preemergence with a nonphytotoxic solvent solution of the compounds of Table 9. Other batches of seeds and tubers for all of the foregoing weed and crop plants were planted at the same time as controls. The control plantings were untreated; i.e., neither any compound nor any solvent was applied. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliate leaf expanding, crabgrass with two leaves, barnyardgrass with two leaves, wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory with four leaves (including the cotyledonary ones), cocklebur with four leaves (including the cotyledonary ones), sorghum with four leaves, corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed with a nonphytotoxic solvent solution of the compounds of Table 9. Other groups of all the same weed and crop plants were sprayed with the same nonphytotoxic solvent so as to provide control plants. Preemergence and postemergence treated plants and controls were mantained in a greenhouse for sixteen days, then all treated plants were compared with their respective controls and rated visually for response to treatment. The data in Table 9 indicate that certain of the compounds of this invention have utility for selective post-emergence weed control in wheat.

                                      TABLE 9                                      __________________________________________________________________________                     ##STR97##                                                                                      ##STR98##                                                                                      ##STR99##                                      ##STR100##                                                                                     ##STR101##                                                                                     ##STR102##                     kg/ha          2               2               2                               __________________________________________________________________________     POST EMERGENCE                                                                 BUSH BEAN      7D,8G,6Y        3G,4C,6Y        3C,4G,6Y                        COTTON         4C,9G           2C,3H,6G        2C,5G                           MORNING GLORY  10C             10C             7C                              COCKLEBUR      10C             2C,7G           3C,7G                           CASSIA         2C,7G           2C,6G           2C,7G                           NUTSEDGE       8G              2C,7G           2G                              CRABGRASS      1C,4G           6G              4G                              BARNYARD GRASS 2C,8H           3C,7H           2H                              WILD OATS      4G              2G              0                               WHEAT          3G              2G              0                               CORN           1C,5G           3C,6G           2C                              SOYBEAN        5H,7G           9C              2H,6G                           RICE           5G              2C,5G           1C                              SORGHUM        7G              3C,7G           0                               PRE EMERGENCE                                                                  MORNING GLORY  9G              9G              8G                              COCKLEBUR      8G              8G              7G                              CASSIA         9G              9G              4G                              NUTSEDGE       10E             10E             9G                              CRABGRASS      7G              8G              3G                              BARNYARD GRASS 8G              3C,9H           1C                              WILD OATS      4G              6G              0                               WHEAT          5G              8G              3G                              CORN           9H              9G              2C,4G                           SOYBEAN        8H              9H              3H                              RICE           10E             9H              6G                              SORGHUM        9H              2C,9G           3G                              __________________________________________________________________________                     ##STR103##                                                                                     ##STR104##                                                                                     ##STR105##                                     ##STR106##                                                                                     ##STR107##                                                                                     ##STR108##                     kg/ha          2               2               2                               __________________________________________________________________________     POST EMERGENCE                                                                 BUSH BEAN      --              --              3C,8G,6Y                        COTTON         9C              9C,5C           --                              MORNING GLORY  9C              10C             1C,9G                           COCKLEBUR      9C              10C             1C,7G                           CASSIA         9C              10C             8H                              NUTSEDGE       5C              8C              9G                              CRABGRASS      9C              8C              2C,8G                           BARNYARD GRASS 9C              9C              9H                              WILD OATS      9C              9C              0                               WHEAT          9C              9C              0                               CORN           10C             10C             2H,8G                           SOYBEAN        9C              3C,8G           2H,9G                           RICE           5C,8G           5C,7G           2C,8G                           SORGHUM        7C              5C,9G           9H                              PRE EMERGENCE                                                                  MORNING GLORY  10E             9G              9G                              COCKLEBUR      8G              9C              9G                              CASSIA         9G              9C              8G                              NUTSEDGE       10E             10E             10E                             CRABGRASS      10E             10E             3G                              BARNYARD GRASS 9H              9H              9H                              WILD OATS      9C              3C,8G           6G                              WHEAT          9H              9H              6G                              CORN           10E             9H              2U,4G                           SOYBEAN        9H              9H              6H                              RICE           10E             10E             10E                             SORGHUM        9H              9E              9H                              __________________________________________________________________________                     ##STR109##                                                                                             ##STR110##                                             ##STR111##                                                                                             ##STR112##                             kg/ha          2                       2                                       __________________________________________________________________________     POST EMERGENCE                                                                 BUSH BEAN      8C,9G                   9C                                      COTTON         --                      2C,2H,9G                                MORNING GLORY  9C                      2H,7G                                   COCKLEBUR      5C,8G                   1C,5G                                   CASSIA         8C                      5C,9G                                   NUTSEDGE       7G                      1C,8G                                   CRABGRASS      6G                      10C                                     BARNYARD GRASS 5C,9H                   10C                                     WILD OATS      2C,8G                   2C,9G                                   WHEAT          3C,7G                   2C,8G                                   CORN           7U,9G                   2C,9G                                   SOYBEAN        9C                      1C,9G                                   RICE           3C,8G                   5C,9G                                   SORGHUM        1U,8G                   2U,9G                                   PRE EMERGENCE                                                                  MORNING GLORY  9H                      9G                                      COCKLEBUR      8G                      10E                                     CASSIA         8G                      10E                                     NUTSEDGE       9G                      10E                                     CRABGRASS      6G                      10E                                     BARNYARD GRASS 9H                      3C,9H                                   WILD OATS      2C,8G                   2C,9H                                   WHEAT          9H                      9H                                      CORN           10E                     10E                                     SOYBEAN        9H                      9H                                      RICE           10E                     10E                                     SORGHUM        9H                      10C                                     __________________________________________________________________________                     ##STR113##                                                     kg/ha          2                       0.4                                     __________________________________________________________________________     POST EMERGENCE                                                                 BUSH BEAN      4S,3H,8G                3S,3H,8G                                COTTON         3C,9G                   2C,8G                                   MORNING GLORY  10C                     10C                                     COCKLEBUR      8G                      2C,7G                                   CASSIA         2C,9G                   3C                                      NUTSEDGE       1C,8G                   8G                                      CRABGRASS      5G                      4G                                      BARNYARD GRASS 2C,9H                   1C,4H                                   WILD OATS      4G                      0                                       WHEAT          6G                      0                                       CORN           1C,9G                   2H,9G                                   SOYBEAN        5C,9G                   9C                                      RICE           5C,9G                   3C,9G                                   SORGHUM        2C,9G                   1C,9G                                   PRE EMERGENCE                                                                  MORNING GLORY  9G                      7G                                      COCKLEBUR      7G                      6G                                      CASSIA         7G                      8G                                      NUTSEDGE       10E                     9G                                      CRABGRASS      6G                      3G                                      BARNYARD GRASS 2C,9H                   1C,8G                                   WILD OATS      5G                      3G                                      WHEAT          9G                      7G                                      CORN           10E                     9G                                      SOYBEAN        9G                      9G                                      RICE           10E                     10E                                     SORGHUM        9G                      9G                                      __________________________________________________________________________

TEST PROCEDURE B

Two bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with seeds of corn, sorghum, Kentucky bluegrass and several grassy weeds. The other pan was planted with seeds of cotton and soybeans, purple nutsedge tubers (Cyperus rotundus), and seeds of several broadleaf weeds. Seeds of the following grassy and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), giant foxtail (Setaria faberii), dallisgrass (Paspalum dilatatum), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pennsylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), cassia (Cassia tora), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A smaller pot was also filled with prepared soil and planted with rice and wheat seeds. Another small pot was planted with seeds of sugarbeets. The above four containers were treated preemergence with nonphytotoxic solvent solutions of the compound of Table 10 (i.e., solutions of compounds were sprayed on the soil surface before seed germination). Duplicates of the above-described seeded containers were prepared without treatment and used as controls.

Twenty-eight days after treatment, the treated and control plants were evaluated and the data recorded as set forth in Table 10. Note that the data indicate that certain compounds of this invention are useful for weed control in crops such as soybeans and wheat.

                  TABLE 10                                                         ______________________________________                                         PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                         ______________________________________                                          ##STR114##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Crabgrass 10C               10C                                                Barnyardgrass                                                                            8G,8C             10C                                                Sorghum   9G,9C             10C                                                Wild Oats 4G,3C             8G,5C                                              Johnsongrass                                                                             8G,5C             10C                                                Dallisgrass                                                                              8G,5C             10C                                                Giant Foxtail                                                                            8G,6C             10C                                                Ky. Bluegrass                                                                            10C               10C                                                Cheatgrass                                                                               10C               10C                                                Sugarbeets                                                                               10C               10C                                                Corn      8G,8H             10C                                                Mustard   10C               10C                                                Cocklebur 2G                7G                                                 Pigweed   10E               10E                                                Nutsedge  4G                9G                                                 Cotton    5G,3H             7G,5H                                              Morningglory                                                                             5G                8G                                                 Cassia    5G                8G,9C                                              Teaweed   5G,3C             9G,8C                                              Velvetleaf                                                                               5G                9G,9C                                              Jimsonweed                                                                               5G                9G,9C                                              Soybean   2G                8G,5H                                              Rice      9G,9C             10C                                                Wheat     7G,4C             10C                                                ______________________________________                                          ##STR115##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Crabgrass 5G                7G                                                 Barnyardgrass                                                                            8G,9C             10C                                                Sorghum   7G,8C             10C                                                Wild Oats 4G                8G,5C                                              Johnsongrass                                                                             8G,5C             9G,5C                                              Dallisgrass                                                                              7G                8G,5C                                              Giant Foxtail                                                                            7G,4C             9G,8C                                              Ky. Bluegrass                                                                            6G,3C             8G,8C                                              Cheatgrass                                                                               8G,3C             8G,3C                                              Sugarbeets                                                                               10C               10C                                                Corn      8G,8H             9G,9H                                              Mustard   10C               10C                                                Cocklebur 4G                8G,5H                                              Pigweed   10E               10E                                                Nutsedge  10E               10E                                                Cotton    7G                7G                                                 Morningglory                                                                             7G                8G,3H                                              Cassia    6G                8G,5C                                              Teaweed   6G,3C             8G,8C                                              Velvetleaf                                                                               6G                10C                                                Jimsonweed                                                                               6G                10C                                                Soybean   7G,5H             8G,5H                                              Rice      9G,9C             10C                                                Wheat     4G                7G,3C                                              ______________________________________                                          ##STR116##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Crabgrass 0                 3G                                                 Barnyardgrass                                                                            4G                6G                                                 Sorghum   3G                7G                                                 Wild Oats 2G                4G                                                 Johnsongrass                                                                             0                 7G                                                 Dallisgrass                                                                              0                 0                                                  Giant Foxtail                                                                            0                 4G                                                 Ky. Bluegrass                                                                            0                 5G                                                 Cheatgrass                                                                               0                 5G                                                 Sugarbeets                                                                               8G,5C             9G,8C                                              Corn      3G                7G                                                 Mustard   --                --                                                 Cocklebur 6G                5G                                                 Pigweed   --                --                                                 Nutsedge  7G                5G                                                 Cotton    --                --                                                 Morningglory                                                                             5G                5G                                                 Cassia    --                --                                                 Teaweed   --                --                                                 Velvetleaf                                                                               --                --                                                 Jimsonweed                                                                               3G                5G                                                 Soybean   5G                7G,5H                                              Rice      7G                10C                                                Wheat     0                 0                                                  ______________________________________                                          ##STR117##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Crabgrass 0                 5G                                                 Barnyardgrass                                                                            8G,8H             10C                                                Sorghum   8G,8H             10C                                                Wild Oats 5G,3H             5G                                                 Johnsongrass                                                                             7G,5H             10C                                                Dallisgrass                                                                              4G                10E                                                Giant Foxtail                                                                            6G                10C                                                Ky. bluegrass                                                                            8G                10E                                                Cheatgrass                                                                               8C,5H             10C                                                Sugarbeets                                                                               4G                8G,5H                                              Corn      7G,5H             10C                                                Mustard   8G                10C                                                Cocklebur 0                 0                                                  Pigweed   10C               10C                                                Nutsedge  0                 0                                                  Cotton    --                --                                                 Morningglory                                                                             0                 3G                                                 Cassia    0                 8G                                                 Teaweed   0                 3G                                                 Velvetleaf                                                                               --                --                                                 Jimsonweed                                                                               0                 4G                                                 Soybean   0                 2G                                                 Rice      7G,5H             10C                                                Wheat     5G                7G                                                 ______________________________________                                    

TEST PROCEDURE C

Pots filled with Fallsington silt loam were planted to soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), cassia (Cassia tora), morningglory (Ipomoea spp.), jimsonweed (Datura stramonium), cocklebur (Xanthium pennsylvanicum), crabgrass (digitaria spp.), nutsedge (Cyperus rotunda), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii), and wild oats (Avena fatua). Approximately 21/2 weeks after planting, the young plants and the soil around them were sprayed overall with the compounds of Table 11 dissolved in a nonphytotoxic solvent. Other groups of all the same weed and crop plants were sprayed with the same nonphytotoxic solvent so as to provide control plants. Fourteen days after treatment, all treated plants were compared with the nonphytotoxic solvent controls and visually rated for response to treatment to give the data presented in Table 11. The data indicate that several of the compounds tested by this procedure are useful for the post-emergence control of weeds in wheat.

                  TABLE 11                                                         ______________________________________                                         OVER THE TOP SOIL/FOLIAGE TREATMENT                                            ______________________________________                                          ##STR118##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Soybeans  10C               10C                                                Velvetleaf                                                                               10G,7C            10G,9C                                             Sesbania  10C               10C                                                Cassia    5G,3C             10G,7C                                             Cotton    8G,5C             10G,7C                                             Morningglory                                                                             5G,5C             10C                                                Alfalfa   10G,7C            10G,9C                                             Jimsonweed                                                                               5G,3C             10C                                                Cocklebur 3G                5G,3C                                              Corn      10G,9C            10G,9C                                             Crabgrass 10G,7C            10G,5C                                             Rice      10G,4C            10G,6C                                             Nutsedge  4G                7G                                                 Barnyardgrass                                                                            10C               10G,6C                                             Wheat     10G,4C            10G,2C                                             Giant Foxtail                                                                            10G,3C            10G,6C                                             Wild Oats 10G,3C            10G,6C                                             Sorghum   10G,8C            10G,6C                                             ______________________________________                                          ##STR119##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Soybeans  10C               10C                                                Velvetleaf                                                                               10C               10C                                                Sesbania  10C               10C                                                Cassia    10G,5C            10G,6C                                             Cotton    10G,3C            8G,5C                                              Morningglory                                                                             9G,3C             10C                                                Alfalfa   10G,9C            10G,9C                                             Jimsonweed                                                                               10C               10C                                                Cocklebur 10G,7C            10G,7C                                             Corn      10G,7C            10G,9C                                             Crabgrass 10G,6C            10G,9C                                             Rice      10G,7C            7G,4C                                              Nutsedge  7G                7G                                                 Barnyardgrass                                                                            10C               10G,7C                                             Wheat     6G                7G,2C                                              Giant Foxtail                                                                            10G,5C            10G,3C                                             Wild Oats 10G,3C            8G,2C                                              Sorghum   10G,5C            10G,9C                                             ______________________________________                                          ##STR120##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Soybeans  8G,2C             10G,4C                                             Velvetleaf                                                                               0                 5G                                                 Sesbania  0                 5G,2C                                              Cassia    3H                3G,5H                                              Cotton    3G                3G                                                 Morningglory                                                                             0                 6G                                                 Alfalfa   0                 7G                                                 Jimsonweed                                                                               0                 7G,4C                                              Cocklebur 0                 3G,2C                                              Corn      3G,2H             8G,5H                                              Crabgrass 0                 3G                                                 Rice      0                 0                                                  Nutsedge  0                 0                                                  Barnyardgrass                                                                            5G                8G                                                 Wheat     0                 0                                                  Giant Foxtail                                                                            0                 3G                                                 Wild Oats 0                 0                                                  Sorghum   5G,3H             7G,3H                                              ______________________________________                                          ##STR121##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Soybeans  10G,6C            10G,7C                                             Velvetleaf                                                                               5G,2C             10G,5H                                             Sesbania  10G,5C            10G,8C                                             Cassia    10G,4C            10G,6C                                             Cotton    8G,2C             10C                                                Morningglory                                                                             6G                8G,2C                                              Alfalfa   4G                10G,4C                                             Jimsonweed                                                                               7G,2C             9G,3H                                              Cocklebur 3G                5G                                                 Corn      7G                8G                                                 Crabgrass 0                 5G                                                 Rice      10G               10G,2C                                             Nutsedge  0                 0                                                  Barnyardgrass                                                                            10G               10G,4C                                             Wheat     0                 7G                                                 Giant Foxtail                                                                            5G                10G,3C                                             Wild Oats 0                 8G,3C                                              Sorghum   10G               10G,3C                                             ______________________________________                                          ##STR122##                                                                    Rate kg/ha                                                                               1/16              1/4                                                ______________________________________                                         Soybeans  2G,3B             5G,3B                                              Velvetleaf                                                                               2G                5G                                                 Sesbania  10G,2C            10G,5C                                             Cassia    0                 5G                                                 Cotton    4G                6G                                                 Morningglory                                                                             0                 0                                                  Alfalfa   5G                5G                                                 Jimsonweed                                                                               2G                4G                                                 Cocklebur 0                 0                                                  Corn      10G,3C            10G,4C                                             Crabgrass 3G                4G                                                 Rice      7G                5G,2C                                              Nutsedge  0                 3G                                                 Barnyardgrass                                                                            8G,3C             10G,4C                                             Wheat     8G,3C             10G,3C                                             Giant Foxtail                                                                            6G                10G                                                Wild Oats 6G                10G,3C                                             Sorghum   8G,2C             10G,3C                                             ______________________________________                                     

What is claimed is:
 1. A compound, or an agriculturally acceptable salt thereof, which has the formula: ##STR123## wherein R is ##STR124## R₁ and R₂ are independently H or CH₃ ; R₃ is --CH₂ CF₃, --CH₂ CH₂ OR₆, --CH₂ CO₂ R₆, ##STR125## --CH₂ CH₂ --CH₂ OR₆ or --CH₂ CH₂ CO₂ R₆ ;R₄ is Cl, Br, F, NO₂, CH₃, --OCH₃, CF₃, or ##STR126## R₅ is H, Cl, Br, F, CH₃ or --OCH₃ ; R₆ is CH₃ or CH₂ CH₃ ; n is 0, 1 or 2; X is CH₃ or --OCH₃ ; W and Y are independently O or S; and Z is CH or N;provided that (a) when R₃ is --CH₂ CF₃, Y is O; and (b) when R₃ is --CH₂ CH₂ OCH₃ and either or both of R₁ and R₂ is CH₃, Y is S.
 2. A compound of claim 1 wherein R₁ and R₂ are hydrogen and W is oxygen.
 3. A compound of claim 2 wherein R is ##STR127##
 4. A compound of claim 3 wherein R₅ is H of Cl.
 5. A compound of claim 4 wherein R₄ is Cl or NO₂.
 6. A compound of claim 5 wherein R₅ is H.
 7. A compound of any one of claims 1 through 6 inclusive wherein Y is O.
 8. The compound of claim 1 which is N-[[4-(2-methoxyethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide.
 9. The compound of claim 1 which is N-[[4-(2,2,2-trifluoroethoxy)-6-methylpyrimidin-2-yl]aminocarbonyl]-2-nitrobenzenesulfonamide.
 10. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 11. a composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 14. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 15. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
 16. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 17. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
 18. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 9 and at least one of the following: surfactant, solid or liquid diluent.
 19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 22. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 23. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 5. 24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 6. 25. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 7. 26. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim
 8. 27. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim
 9. 